JPH02107639A - ベンザルマロン酸エステル官能基を含有するジオルガノポリシロキサン - Google Patents
ベンザルマロン酸エステル官能基を含有するジオルガノポリシロキサンInfo
- Publication number
- JPH02107639A JPH02107639A JP1227630A JP22763089A JPH02107639A JP H02107639 A JPH02107639 A JP H02107639A JP 1227630 A JP1227630 A JP 1227630A JP 22763089 A JP22763089 A JP 22763089A JP H02107639 A JPH02107639 A JP H02107639A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- groups
- following formula
- formulas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 title abstract description 12
- ISDGWTZFJKFKMO-UHFFFAOYSA-N 2-phenyl-1,3-dioxane-4,6-dione Chemical group O1C(=O)CC(=O)OC1C1=CC=CC=C1 ISDGWTZFJKFKMO-UHFFFAOYSA-N 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- -1 trimethylsilyloxy group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 11
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000000314 lubricant Substances 0.000 abstract description 3
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical group OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 25
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 239000002966 varnish Substances 0.000 description 11
- 239000013598 vector Substances 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 238000002211 ultraviolet spectrum Methods 0.000 description 9
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000013307 optical fiber Substances 0.000 description 3
- 239000010502 orange oil Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical group CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 2
- FBLUJEZNJVZMKK-UHFFFAOYSA-N 3,4-dimethoxy-5-prop-2-enylbenzaldehyde Chemical compound COC1=CC(C=O)=CC(CC=C)=C1OC FBLUJEZNJVZMKK-UHFFFAOYSA-N 0.000 description 2
- IJGXTTPJTDSRBO-UHFFFAOYSA-N 4-hydroxy-3-methoxy-5-prop-2-enylbenzaldehyde Chemical compound COC1=CC(C=O)=CC(CC=C)=C1O IJGXTTPJTDSRBO-UHFFFAOYSA-N 0.000 description 2
- KBXMYFVAWMPGAT-UHFFFAOYSA-N 4-methoxy-3-prop-2-enylbenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1CC=C KBXMYFVAWMPGAT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- BCINBJDCXBFCDT-UHFFFAOYSA-N 1-methoxy-2-prop-2-enylbenzene Chemical compound COC1=CC=CC=C1CC=C BCINBJDCXBFCDT-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DGWCHURQYFMBFC-UHFFFAOYSA-N 3-methoxy-4-prop-2-enoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1OCC=C DGWCHURQYFMBFC-UHFFFAOYSA-N 0.000 description 1
- DUUDAGLUGZXHRC-UHFFFAOYSA-N 4-butoxy-3-methoxy-5-prop-2-enylbenzaldehyde Chemical compound CCCCOC1=C(CC=C)C=C(C=O)C=C1OC DUUDAGLUGZXHRC-UHFFFAOYSA-N 0.000 description 1
- HDZJQLIQQWIJBW-UHFFFAOYSA-N 4-hydroxy-3-prop-2-enylbenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1CC=C HDZJQLIQQWIJBW-UHFFFAOYSA-N 0.000 description 1
- TYNJQOJWNMZQFZ-UHFFFAOYSA-N 4-prop-2-enoxybenzaldehyde Chemical compound C=CCOC1=CC=C(C=O)C=C1 TYNJQOJWNMZQFZ-UHFFFAOYSA-N 0.000 description 1
- 101100018369 Arabidopsis thaliana ICR3 gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical group CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- 101000957333 Homo sapiens Muscleblind-like protein 3 Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 102100038751 Muscleblind-like protein 3 Human genes 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- YSRBRMMHTQOUDW-UHFFFAOYSA-N bis(2-ethylhexyl) propanedioate Chemical compound CCCCC(CC)COC(=O)CC(=O)OCC(CC)CCCC YSRBRMMHTQOUDW-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- IXLBCTIKPQLNFD-UHFFFAOYSA-M potassium;butan-1-ol;hydroxide Chemical compound [OH-].[K+].CCCCO IXLBCTIKPQLNFD-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31609—Particulate metal or metal compound-containing
- Y10T428/31612—As silicone, silane or siloxane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR88/12016 | 1988-09-09 | ||
| FR8812016A FR2636338B1 (fr) | 1988-09-09 | 1988-09-09 | Diorganopolysiloxane a fonction benzalmalonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02107639A true JPH02107639A (ja) | 1990-04-19 |
| JPH055857B2 JPH055857B2 (de) | 1993-01-25 |
Family
ID=9370002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1227630A Granted JPH02107639A (ja) | 1988-09-09 | 1989-09-04 | ベンザルマロン酸エステル官能基を含有するジオルガノポリシロキサン |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5053290A (de) |
| EP (1) | EP0358584B1 (de) |
| JP (1) | JPH02107639A (de) |
| AT (1) | ATE80636T1 (de) |
| AU (1) | AU4113889A (de) |
| BR (1) | BR8904492A (de) |
| DE (1) | DE68902899D1 (de) |
| FR (1) | FR2636338B1 (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0446933A (ja) * | 1990-06-15 | 1992-02-17 | Shin Etsu Chem Co Ltd | 有機変性シリコーンオイルの製造方法 |
| JP2005524750A (ja) * | 2002-05-09 | 2005-08-18 | ザ プロクター アンド ギャンブル カンパニー | 表面を疎水性に改質し及びそれにより処理される表面への活性剤の送達を高めるための陰イオン性官能化ポリオルガノシロキサンを含む組成物 |
| JP2005533141A (ja) * | 2002-07-16 | 2005-11-04 | ディーエスエム アイピー アセッツ ビー．ブイ． | サンスクリーン |
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| FR2642967B1 (fr) * | 1989-02-15 | 1991-06-07 | Oreal | Utilisation en cosmetique de diorganopolysiloxanes a fonction benzalmalonate et nouvelles compositions cosmetiques contenant ces composes, destinees a la protection de la peau et des cheveux |
| GB9110123D0 (en) * | 1991-05-10 | 1991-07-03 | Dow Corning | Organosilicon compounds their preparation and use |
| US5296625A (en) * | 1991-11-06 | 1994-03-22 | Siltech Inc. | Silicone alkoxylated esters carboxylates |
| FR2725448B1 (fr) * | 1994-10-07 | 1997-01-03 | Oreal | Nouveaux filtres solaires, compositions cosmetiques photoprotectrices les contenant et utilisations |
| IL115558A (en) | 1994-10-14 | 2000-01-31 | Givaudan Roure Int | Photostable cosmetic light-screening compositions comprising organosiloxane derivatives |
| FR2756287B1 (fr) * | 1996-11-28 | 1998-12-24 | Oreal | Nouveaux derives de filtres silicies sur leur partie aromatique, compositions cosmetiques photoprotectrices les contenant et utilisations |
| US6018044A (en) * | 1998-01-02 | 2000-01-25 | Roche Vitamins Inc. | Light screening compositions |
| DE69930796T2 (de) * | 1998-07-16 | 2006-10-26 | Dsm Ip Assets B.V. | Lichtschutzmittelzusammensetzung enthaltend ein UV-B-Lichtschutzmittel vom Polysiloxan-Typ und ein UV-B-Lichtschutzmittel vom Benzimidazol-Typ |
| DE10026432A1 (de) | 2000-05-29 | 2002-02-14 | 3M Espe Ag | Präpolymere (Meth)acrylate mit polycyclischen oder aromatischen Segmenten |
| US20070190325A1 (en) | 2003-12-04 | 2007-08-16 | Katja Berg-Schultz | Microcapsules with uv filter activity and process for producing them |
| AU2005226922B2 (en) | 2004-03-25 | 2010-03-04 | Dsm Ip Assets B.V. | UV absorbing chromophores covalently bonded to hyperbranched polymers |
| JP4921351B2 (ja) | 2004-03-26 | 2012-04-25 | ディーエスエム アイピー アセッツ ビー．ブイ． | レチノイドと組み合せたｈｄａｃインヒビターを含む組成物 |
| WO2006000350A2 (en) | 2004-06-28 | 2006-01-05 | Dsm Ip Assets B.V. | Cosmetic compositions containing protein hydrolysates |
| CN101203278A (zh) * | 2005-04-19 | 2008-06-18 | 默克专利股份有限公司 | 紫外线保护 |
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| EP1959914B1 (de) | 2005-12-09 | 2014-05-21 | DSM IP Assets B.V. | Kosmetische oder dermatologische zusammensetzungen mit modifizierten titandioxid-teilchen |
| EP2034977B1 (de) | 2006-04-21 | 2011-07-13 | DSM IP Assets B.V. | Verwendung von opioid-rezeptor-antagonisten |
| CN101505712B (zh) | 2006-06-16 | 2013-03-20 | 帝斯曼知识产权资产管理有限公司 | 基于超支化缩合聚合物的组合物以及超支化缩合聚合物 |
| US20100055218A1 (en) | 2006-07-14 | 2010-03-04 | Daniel Raederstorff | Novel compositions |
| EP1952845A1 (de) | 2007-01-26 | 2008-08-06 | DSMIP Assets B.V. | Verwendung eines Astaxathinderivats für kosmetische Zwecke |
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| ATE544805T1 (de) | 2008-12-01 | 2012-02-15 | Dsm Ip Assets Bv | Neuer prozess |
| US20110300240A1 (en) | 2009-02-23 | 2011-12-08 | Daniel Raederstorff | Cajanus extracts and glucosamine for inflammatory disorders |
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| JP2013513572A (ja) | 2009-12-09 | 2013-04-22 | ディーエスエム アイピー アセッツ ビー．ブイ． | 新規化合物 |
| US20130004437A1 (en) | 2009-12-09 | 2013-01-03 | Alexander Schlifke-Poschalko | Novel compound |
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| CN102656208A (zh) | 2009-12-09 | 2012-09-05 | 帝斯曼知识产权资产管理有限公司 | 通过氧杂环丁烷的聚合而制备的吸收紫外线的树枝状聚醚 |
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| ES2659407T3 (es) | 2010-07-23 | 2018-03-15 | Dsm Ip Assets B.V. | Uso tópico de esteviol o isoesteviol en el cuidado capilar |
| US20140044656A1 (en) | 2011-03-01 | 2014-02-13 | Dsm Ip Assets B.V. | Novel use |
| EP2522331A1 (de) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Verwendung von Resveratrol und Niacinamid |
| EP2522335A1 (de) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Verwendung von Resveratrol und Natriumascorbylphosphat |
| EP2522330A1 (de) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Verwendung von Rsveratrol und einem Edelweiss-Extrakt |
| EP2522328A1 (de) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Verwendung von Resveratrol und Ascorbyl-2-Glucosid |
| EP2522329A1 (de) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Verwendung von Resveratrol und Arbutin |
| EP2522332A1 (de) | 2011-05-09 | 2012-11-14 | DSM IP Assets B.V. | Verwendung von Resveratrol und Magnesiumascorbylphosphat |
| WO2013041515A1 (en) | 2011-09-20 | 2013-03-28 | Dsm Ip Assets B.V. | Novel polyester based uv filters |
| KR102003093B1 (ko) | 2012-01-09 | 2019-07-23 | 디에스엠 아이피 어셋츠 비.브이. | 스킨 케어에 있어서 다니엘론 및 그의 유도체의 용도 |
| EP2623094A1 (de) | 2012-02-02 | 2013-08-07 | DSM IP Assets B.V. | Verwendung von Edelweiss-Extrakt |
| WO2015049366A1 (en) | 2013-10-04 | 2015-04-09 | Dsm Ip Assets B.V. | Skin tanning extract |
| EP2873414A1 (de) | 2013-11-19 | 2015-05-20 | DSM IP Assets B.V. | Verwendung eines Edelweissextrakts in der Haarpflege zur Vorbeugung von Haarergrauung |
| EP2873440A1 (de) | 2013-11-19 | 2015-05-20 | DSM IP Assets B.V. | Verwendung eines Edelweissextrakts in der Haarpflege zur Stimulierung des Haarwuchses |
| AR100211A1 (es) | 2014-05-19 | 2016-09-21 | Interquim Sa | Procedimiento para la preparación de un polímero fotoprotector progresivo de organosilicio; polímero fotoprotector progresivo de organosilicio, su uso, composición que lo comprende, monómero precursor, procedimientos para la preparación de dicho monómero precursor |
| ES2776411T3 (es) | 2014-10-17 | 2020-07-30 | Dsm Ip Assets Bv | Uso de una composición cosmética que comprende ácido 10-hidroxiesteárico |
| WO2016090081A1 (en) | 2014-12-04 | 2016-06-09 | Lubrizol Advanced Materials, Inc. | Viscosity modification of organic phase containing compositions |
| EP3421096A1 (de) | 2017-06-30 | 2019-01-02 | Athenion AG | Verfahren zur solubilisierung von schwer wasserlöslichen kosmetischen mitteln |
| EP3709956B1 (de) | 2017-11-13 | 2024-10-23 | DSM IP Assets B.V. | Kosmetische oder dermatologische zusammensetzungen |
| BR112020012422B1 (pt) | 2017-12-19 | 2023-12-26 | Dsm Ip Assets B.V | Composição tópica, uso relacionado e método para reduzir a transferência de gordura ou óleo para uma superfície |
| US20210077376A1 (en) | 2017-12-19 | 2021-03-18 | Dsm Ip Assets B.V. | Topical composition |
| KR20220018002A (ko) * | 2019-06-07 | 2022-02-14 | 디에스엠 아이피 어셋츠 비.브이. | 국소 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4405469A (en) * | 1978-03-08 | 1983-09-20 | Consortium Fur Elektrochemische Ind. Gmbh | Greases prepared from organosiloxanes with SiC-bonded groups |
| US4242383A (en) * | 1979-04-18 | 1980-12-30 | General Electric Company | Method of providing a polycarbonate article with a uniform and durable organopolysiloxane coating |
| FR2602776B1 (fr) * | 1986-08-12 | 1988-11-10 | Rhone Poulenc Chimie | Diorganopolysiloxane a fonction beta-cetoester utile comme stabilisant des polymeres a base de polychlorure de vinyle |
| FR2625210B1 (fr) * | 1987-12-29 | 1990-05-18 | Rhone Poulenc Chimie | Diorganopolysiloxane a fonction benzylidene-3 camphre |
-
1988
- 1988-09-09 FR FR8812016A patent/FR2636338B1/fr not_active Expired - Lifetime
-
1989
- 1989-09-04 JP JP1227630A patent/JPH02107639A/ja active Granted
- 1989-09-06 BR BR898904492A patent/BR8904492A/pt unknown
- 1989-09-07 AU AU41138/89A patent/AU4113889A/en not_active Abandoned
- 1989-09-08 DE DE8989420329T patent/DE68902899D1/de not_active Expired - Lifetime
- 1989-09-08 EP EP89420329A patent/EP0358584B1/de not_active Expired - Lifetime
- 1989-09-08 AT AT89420329T patent/ATE80636T1/de not_active IP Right Cessation
- 1989-09-11 US US07/405,299 patent/US5053290A/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0446933A (ja) * | 1990-06-15 | 1992-02-17 | Shin Etsu Chem Co Ltd | 有機変性シリコーンオイルの製造方法 |
| JP2005524750A (ja) * | 2002-05-09 | 2005-08-18 | ザ プロクター アンド ギャンブル カンパニー | 表面を疎水性に改質し及びそれにより処理される表面への活性剤の送達を高めるための陰イオン性官能化ポリオルガノシロキサンを含む組成物 |
| JP2005533141A (ja) * | 2002-07-16 | 2005-11-04 | ディーエスエム アイピー アセッツ ビー．ブイ． | サンスクリーン |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2636338B1 (fr) | 1990-11-23 |
| FR2636338A1 (fr) | 1990-03-16 |
| EP0358584B1 (de) | 1992-09-16 |
| ATE80636T1 (de) | 1992-10-15 |
| DE68902899D1 (de) | 1992-10-22 |
| US5053290A (en) | 1991-10-01 |
| JPH055857B2 (de) | 1993-01-25 |
| BR8904492A (pt) | 1990-04-24 |
| AU4113889A (en) | 1990-03-15 |
| EP0358584A1 (de) | 1990-03-14 |
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